Despite a stellar career, Gary Rosenberg claims, “I never worked a day in my life”

“The hotel business is just a matter of inviting someone into your home, giving them a good meal and a nice place to sleep and inviting them back again.”
Gary Rosenberg


Gary’s dad, Rosie, owned The 520, a small bar in Chester, PA, near Philly. “It was Cheers. Same bar, same stools, same customers,” Gary says. A local businessman offered Rosie the chance to run the bar in the new Colony Hotel. Rosie accepted and sold The 520.

Man pours; God laughs. 2 months later, Rosie suffered a fatal stroke behind his new bar. He was 49. Gary, 13.

“I was devastated. He was my best friend. I immediately knew the man I
wanted to be.“

Gary “grew up” in hospitality. As a teen, he bused tables at the Colony. Waitresses paid him a quarter a night. “I noticed the bellmen got $1 a suitcase. I aspired to be a bellman.”

He did considerably better. His career would make most golfers tee-to-green with envy…

In 1977, a major snowstorm closed PA schools down. Gary’s best friend, a school teacher, invited him on an impromptu visit to his mom in Ft. Lauderdale. He’d never been there before. Both in their 20s, they decided to stay.

Gary had run the Mendenhall Inn on the DuPont estate in Wilmington, Del. In FL, he became assistant GM of the beachfront Bahia Mar Hotel & Yachting Center (with the largest marina in the state). “OMG,” he thought. “I’m so over my head.” A year later, he became GM.

After 5 years, a headhunter called. Arvida, the largest luxury property developer in FL, was building a new resort on Longboat Key. Did Gary want to interview for C.O.O.?

“Yes,” Gary said. “I’ve never been to the Keys.”

He soon learned the FL Keys were 200 plus miles from Longboat Key off the west coast of Sarasota. Arvida needed someone to oversee finishing the resort operation, including the Inn on the Beach and the Harborside Golf Course at the new Longboat Key Resort.

“They tell me you’re the guy,” the CEO said.

“Let’s do this,” Gary said. He moved to Sarasota to open and run his first golf resort. It opened in 1982.

In 5 years, Gary became a regional v.p. Arvida ran luxury resorts, including the Boca Raton Hotel, the Boca Beach Club, Boca West and many golf courses. Sawgrass TPC was a crown jewel. “Sawgrass opened lots of doors,” Gary says.

ClubCorp, then the world’s largest hospitality company, managed 300 golf courses on 6 continents. They were taking over Palmas del Mar in Puerto Rico. Would Gary oversee it?

You bet.

3 years later, Gary moved to Pinehurst, NC. He managed the legendary Pinehurst Golf Club and traveled to France, Scotland and Ireland to work on ClubCorp deals.

But Gary’s heart was in the States.

“I want to run the Homestead,” he told his boss about the once grand hotel and 1500 acre resort that dates back to 1766.

“You’re an idiot,” his boss said.

“You don’t know what the Homestead is. I want to bring it into the next century.”

The Homestead in Hot Springs, VA and the Greenbrier in W. VA are 2 of the most historic hotels in America. Gary lived in Hot Springs for 15 years. “At the first executive staff meeting, I established our mission statement: to kick the Greenbrier’s butt.” Based at the Homestead, he was COO of ClubCorp’s resort group, helping to run famed courses and resorts including Pamilla in Cabo, Barton Creek in Austin, Ocean Reef in Key Largo and Pinehurst.

At the Homestead, Gary became close friends with Sam Snead, one of the greatest golfers ever. He met and golfed with legends including Arnold Palmer.

Gary retired for the first time in 2004. He bought a Harley and spent the next 4 years touring 38 states with wife Kelly (more about her later). A business friend called and asked him to become COO of a hotel group. “Nope,” he said. “I’m ridin’ my Harley.”

6 months later, another call. This time an offer to run Noble Resort Group. By then, he’d had enough of the vagabond life. He said, “Let’s do this.”

After 5 years, Noble was bought by Interstate, the largest hotel management group in the world. Gary was sr. exec. of the resort group. He worked on plans to carve a golf course out of an old phosphate mine in the middle of nowhere (aka Bowling Green, FL). Streamsong’s now 2 (soon to be 3) courses rank among the country’s top 100 public courses.

In 2012, “I hung it up for real.”

About his career, he says, “I never considered it work. At the Homestead, everyone knew my 3pm appointment was on the first tee. The hotel business is just a matter of inviting someone into your home, giving them a good meal and a nice place to sleep and inviting them back again.”

One night in Virginia made him especially proud. He was soaking in the tub, reading a book by his friend who ran the world’s largest tennis management company. “He wrote about reaching out and getting to know your staff. I realized I didn’t know our midnight crew.”

He dried off, dressed and drove to the resort. Walking down a corridor, he came upon a housekeeper. His name was on his name tag.

“Hi, Steve,” Gary said.

“Mr. Rosenberg, do you have a minute?”

“Sure. Let’s go into the boardroom and sit down.”

In the boardroom, Steve said, “I’ve worked at the Homestead for 25 years. It’s given me the ability to feed my family. I’ve always fed them hamburger. Since you’ve been here, we’re eating steak.”

Gary’s eyes misted over. His nickname at CC was Misty. Every year he took his execs to Las Vegas. Whenever he was introduced to speak, “I’d overhear guys doing the over/under, betting on how long I’d take to tear up.”

And now for the story about Gary and Kelly.

It was 1984. Gary was working at the Longboat Key Resort. Walking past the pro shop, he noticed a striking young brunette behind the counter. “I did a double take. But I was the boss, so I didn’t get too familiar.” A couple of years later, he still hadn’t made his move. One day at Harborside, the first course he’d developed, he scored a hole-in-one. It was July 15, 1984. Hole #3. He walked into the pro shop.

Kelly Churma, the striking brunette, said, “Congratulations, Mr. Rosenberg. I hear you made a hole-in-one.”

“A lightbulb went off,” he says. He walked behind the counter. “Doesn’t that deserve a peck on the cheek?”

Kelly obliged, but thought to herself: I want to call security.

Several months later, Gary had become a regional v.p. and moved to Sawgrass. Driving back to Sarasota one weekend, he thought about how he was no longer Kelly’s immediate boss. Kelly had been promoted, too. She was a real estate broker handling sales and rentals for LBK condos.

He was on I-4, just past the Disney exit. He called Kelly from the car. “I’d love to take you out for dinner tonight.”

Kelly said, “When you get to Longboat, stop in the office. We’ll talk about it.”

At the office, she agreed. “Tell me where you live,” Gary said.

“Tell me where we’re going. I’ll meet you.”

“She made me grovel,” Gary says. They married 5 years after. Gary was 40; Kelly, 25. “30 years later, I’m still paying for that first kiss. With Kelly’s maturity and my lack of it, the marriage works.” They have 3 adult children, Alexis, Andie and Kevin (Gary’s son from an earlier marriage.)

During his career, Gary met and/or golfed with luminaries including Bill Clinton and Gerald Ford. And Gen. Norman Schwarzkopf shortly after Desert Storm. He became dear friends with Tom Landry, coach of the Dallas Cowboys. “If you look up ‘class’ in the dictionary, you’ll find Tom’s picture.”

Gary became close to Dave Thomas, founder of Wendy’s, named for Thomas’ adopted daughter. Thomas, who “enjoyed a little wager on the golf course,” started a foundation to support adoption. “He didn’t finish high school,” Gary says. “He felt he wasn’t a good role model for kids. So in his 90s, he got his GED and walked in graduation with the class at Coconut Creek High School. He was voted Most Likely to Succeed.”

Gary scored his second hole-in-one last year, on #7 of the West Course at Laurel Oak CC in Sarasota. The date was 5.20, a meaningful date for Gary whose dad’s bar was The 520. Gary and Kelly also married on 5.20.

Scoring his 2nd hole-in-one, Gary couldn’t wait to get back into his car and call Kelly with the news.

Her response? “Thank heavens you have a new story.”

(Your dad would be proud, Gary. So are your friends at LOCC. Thanks for sharing your story.)

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